CITA-A, Department of Agricultural Sciences, University of Azores, Rua capitão João d'Ávila - Pico da Urze, 9700-042 Angra do Heroísmo, Azores, Portugal; iMed.UL, Faculty of Pharmacy, University of Lisbon, Av. Prof. Gama Pinto, 1649-003 Lisbon, Portugal.
Phytochemistry. 2013 Nov;95:308-14. doi: 10.1016/j.phytochem.2013.06.019. Epub 2013 Jul 28.
Two unprecedented guaiane-type sesquiterpene glycosides (undulatumosides A and B) were isolated by bioassay-guided fractionation from the MeOH extract of Pittosporum undulatum fruits, along with six known compounds, including the guaiane isomers 5-guaien-11-ol and 4-guaien-11-ol. The structures of the compounds were established as 4-guaiene-11-O-β-d-(3'-angeloxy-6'-deoxy)-glucopyranoside and 1(5)-guaiene-11-O-β-d-(3'-angeloxy-6'-deoxy)-glucopyranoside by spectroscopic methods, including 1D and 2D homo- and heteronuclear NMR experiments (COSY, HSQC, HMBC and NOESY), and HR-mass spectrometry. P. undulatum is a highly invasive weed that often outcompetes other plants, yet its fruits have become a traditional anti-inflammatory medicine in Azores. Therefore, aiming to investigate the claimed properties, the in vitro anti-inflammatory activity of guaiane-type sesquiterpenes was evaluated by analyzing their inhibitory effects on chemical mediators released by the LPS activated RAW 264.7 murine macrophages cell line. In addition, the cytotoxicity of these compounds was also evaluated in this cell line. Undulatumoside A, 5-guaien-11-ol and 4-guaien-11-ol displayed anti-inflammatory activity with IC50 values of 16.4, 8.1 and 7.2μM, respectively, comparable to that of the positive control, indomethacin (IC50=18.2 μM), with no cytotoxic effects (IC50 ≥ 198 μM). Furthermore, the same set of compounds was also assessed for anti-proliferative activity in lung large cell carcinoma COR-L23 and amelanotic melanoma C32 cells.
从李属植物果实的甲醇提取物中，通过生物测定指导的分步分离，分离出两种前所未有的愈创木烷型倍半萜糖苷（undulatumoside A 和 B），以及六种已知化合物，包括愈创木烷异构体 5-愈创木烯-11-醇和 4-愈创木烯-11-醇。通过光谱方法，包括 1D 和 2D 同核和异核 NMR 实验（COSY、HSQC、HMBC 和 NOESY）以及高分辨率质谱，确定了化合物的结构为 4-愈创木烯-11-O-β-d-(3'-当归氧基-6'-去氧）-吡喃葡萄糖苷和 1(5）-愈创木烯-11-O-β-d-(3'-当归氧基-6'-去氧）-吡喃葡萄糖苷。李属植物是一种高度入侵的杂草，常常与其他植物竞争，但它的果实已成为亚速尔群岛的传统抗炎药。因此，为了研究声称的特性，通过分析其对 LPS 激活的 RAW 264.7 鼠巨噬细胞系释放的化学介质的抑制作用，评估了愈创木烷型倍半萜的体外抗炎活性。此外，还在该细胞系中评估了这些化合物的细胞毒性。Undulatumoside A、5-愈创木烯-11-醇和 4-愈创木烯-11-醇显示出抗炎活性，IC50 值分别为 16.4、8.1 和 7.2μM，与阳性对照吲哚美辛（IC50=18.2μM）相当，无细胞毒性（IC50≥198μM）。此外，还评估了同一组化合物在肺大细胞癌 COR-L23 和无黑色素黑色素瘤 C32 细胞中的抗增殖活性。
